3.5-Bis(4-nitrobenzylidene)-1-methyl-4-piperidone

ID: ALA472965

PubChem CID: 10619701

Max Phase: Preclinical

Molecular Formula: C20H17N3O5

Molecular Weight: 379.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C/C(=C\c2ccc([N+](=O)[O-])cc2)C(=O)/C(=C/c2ccc([N+](=O)[O-])cc2)C1

Standard InChI:  InChI=1S/C20H17N3O5/c1-21-12-16(10-14-2-6-18(7-3-14)22(25)26)20(24)17(13-21)11-15-4-8-19(9-5-15)23(27)28/h2-11H,12-13H2,1H3/b16-10+,17-11+

Standard InChI Key:  RZSZIUWKHOTPLG-OTYYAQKOSA-N

Molfile:  

     RDKit          2D

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    5.1081   -8.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3937   -9.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -8.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -8.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3937   -7.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081   -8.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3937   -6.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081   -6.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081   -5.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8226   -5.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3937   -5.2295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5371   -5.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5371   -6.4670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8226   -6.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8226   -4.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5371   -3.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5371   -3.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2515   -2.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9660   -3.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9660   -3.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2515   -4.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3937  -10.1795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081  -10.5920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792  -10.5920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6805   -2.7545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6805   -1.9295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3950   -3.1670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2515   -6.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 13 14  1  0
  5  7  1  0
 10 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  2  0
 21 16  1  0
  2  3  1  0
  9 11  2  0
  8 14  1  0
 22 23  2  0
 22 24  1  0
  2 22  1  0
  5  6  2  0
 10 12  1  0
  6  1  1  0
 25 26  2  0
 25 27  1  0
 19 25  1  0
 12 13  1  0
 13 28  1  0
M  CHG  4  22   1  24  -1  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA472965

   (3E,5E)-1-methyl-3,5-bis[(4-nitrophenyl)methylidene]piperidin-4-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 379.37

Molecular Weight (Monoisotopic): 379.1168

AlogP: 3.48

#Rotatable Bonds: 4

Polar Surface Area: 106.59

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.75

CX LogP: 4.16

CX LogD: 4.16

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: -0.56

References

1. Pati HN, Das U, Das S, Bandy B, De Clercq E, Balzarini J, Kawase M, Sakagami H, Quail JW, Stables JP, Dimmock JR..  (2009)  The cytotoxic properties and preferential toxicity to tumour cells displayed by some 2,4-bis(benzylidene)-8-methyl-8-azabicyclo[3.2.1] octan-3-ones and 3,5-bis(benzylidene)-1-methyl-4-piperidones.,  44  (1): [PMID:18468733] [10.1016/j.ejmech.2008.03.015]

Source

Source(1):

• Scientific Literature